


Carefully Caught Regrets

by propinquitous



Category: Supernatural
Genre: Angst, Gen, Grief/Mourning
Language: English
Status: Completed
Published: 2013-06-23
Updated: 2013-08-06
Packaged: 2017-12-15 21:06:43
Rating: General Audiences
Warnings: Major Character Death
Chapters: 15
Words: 3,367
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/854054
Author URL: https://archiveofourown.org/users/propinquitous/pseuds/propinquitous
Summary: <blockquote class="userstuff">
              <p>A chronicle of Dean's loss in short form.</p>
            </blockquote>





	1. November 12, 1983

**Author's Note:**

> Character deaths all canon, and I did my best to follow established timelines.
> 
> Spoilers through season eight.

Dean wants his mom to come home.  He knows that she won’t.  He is a child but he understands that when a house goes up in flames and your mom fails to follow you out, she never comes home again.

It’s late.  They’re at the Days Inn on Iowa St.  Sam sleeps in a play pen and Dean sleeps alone in a queen-sized bed.  He doesn’t like the unfamiliar scent of the motel quilt or the rough texture of the sheets, but he doesn’t yet know how to articulate this distaste.  Instead his stomach feels tight with homesickness.  All children feel homesick; they all cry at grandma’s house and need to be picked up early from summer camp.  This is different.  It will never go away.  Though he’s not yet five years old, he doesn’t expect it to get better because if he starts crying, there’s no one to call, no one to come get him.  He can’t wake his dad up and ask him to take him home because there’s nowhere to go home to and besides, he knows his dad won’t like his crying.  These are things he knows but cannot yet express.  Children know more than we remember knowing. 

Dean shuts his eyes and fights the tears as they come.


	2. December 25, 1991

Dean doesn’t want Sam to know.  They’re so young but even now he has a profound need to protect Sammy from the things he’s learned.  So, when Sam reads Dad’s journal and finds the truth, Dean doesn’t know what to say.  He sits frozen for a moment.  His mind circles through the usual lies children tell adults - I didn’t know, I don’t remember - before it comes to rest on the lies adults tell children - it’s just a story, it’s all a joke.  In the end he decides that neither approach is better than the truth.  Sam will eventually find out, anyway.  And so he admits that yes, nightmares are real, and nightmares killed Mom.  It awkwardly tumbles off his twelve-year-old tongue, tinged with more regret than any child should be able to feel.  He doesn’t want Sammy to be afraid.  He does his best to assure him that Dad kills the things that lurk and snarl in the shadows, that they are safe in this hotel room, surrounded by salt and iron. He has immense faith in his father.  He believes the words coming out of his mouth.

 Sam is more afraid than he will ever admit.


	3. November 2, 1993

It’s been ten years and it doesn’t hurt like it used to. The pain is different, less acute. It has transformed from something piercing into a dull ache in his chest. His ribcage pulls tighter on holidays and when he’s stuck in bed with the flu, but beyond that his mom usually stays in his emotional periphery. Truth be told, he barely remembers her anymore. Dean feels guilty about it; he doesn’t understand how he can miss someone he doesn’t remember, a mother he hardly had. The smell on his clean clothes is one of the few things that triggers his memory, and he doesn’t know that it’s because John still uses the same brand of detergent.

 _You can’t make homes out of human beings_. He doesn’t remember where he heard it, but he vehemently disagrees. When you have no home, no house on a block with hedges or old screen doors, your only choice is to carve out a space for yourself in the hearts of others. He has Sam and Bobby, and on rare occasions, his dad. They’re enough most days. Still, homesickness lurks somewhere between his stomach and lungs and he has accepted that he is probably never going to feel at home again. Not completely.

He still misses his mom, but it no longer makes him cry. 

**Notes for the Chapter:**

> The quote comes from Warsan Shire's _For Women Who Are Difficult to Love_ , which can be found [here](http://vimeo.com/38766162). It wasn't yet published when this entry takes place.


	4. September 17, 2001

Sam’s voice trembles when he tells Dean that classes start the following week.  He’s trying to sound resolute.  Determination is key.  He’s done with this family, its codependence and obligation.  He loves his brother and his father but he has to look out for himself and he simply can’t be a part of this anymore.  For the first time, the possibility of a normal life seems within his grasp and he is not letting it go out of guilt.  Dean can hold his own.

Dean doesn’t understand; he barely sees beyond the loss.  Taking care of yourself not because others depend on you, but because you simply want to, is not something familiar to him.  What Dean does know is that Sammy is smart.  He can see how badly he wants this, and in retrospect sees how hard he’s worked to get here.  For a moment, the cloud of grief clears and Dean feels unrelentingly proud of his little brother.  He feels ashamed of his selfishness.  It’s just, it never occurred to him that watching out for Sammy would mean letting him out of his sight and even worse, his reach.   His chest tightens at the thought.  The idea of losing Sam weighs down on him, and he knows that he will leave no matter what Dean says.   It’s best to part on good terms, he thinks.  So even though he doesn’t understand it, he lets his brother go.

He hopes Sam will still love him in four years.


	5. November 2, 2003

Twenty years hardly mean a thing and Dean is alone.  He is twenty-four years old and if he weren’t so afraid of flying, he’d have left the country to escape, to put an ocean or at least a border between him and his life.  Though he wants to call Sammy, he doesn’t want to bring him down.  He wants to spare him the renewed burning in his chest.  The pain feels raw and he can’t pinpoint why the wound is suddenly fresh and hot.  

His feelings embarrass him.  If he were more introspective, he would realize that he’s old enough now to be friends with his mom.  He would bring a new girlfriend home and after she left he would look to his mom for approval, and she would smile and then Dean wouldn’t be able to hold back his gushing.  She would be happy that her son found someone smart enough to see through him, and she might tease him about finally finding a girl prettier than him.  If he were the sort to think about these things, he would wonder if he’d still need to be seen through if she hadn’t died, if maybe having his mom around would have left his innate softness more accessible.  If he had been brought up to articulate his feelings, he'd realize that the ache springs from this absence, from all the things he'll never know.

But Dean’s not any of these things, so he holes himself up in a motel in Eagle Pass, Indiana with a handle of Wild Turkey instead.


	6. July 27, 2006

He’s an orphan now. _Orphan_. He tries to shape his lips around the word that suddenly describes him and Sammy but chokes instead. Dean can't make sense of it; the hurt is not what he would have imagined. Where Mom left a seething absence, a longing for things unknowable, Dad has bored a hole of unkept promises, of amends not yet made. It's a different sort of grief. A different sense of loss.

Dean tries to hold on to the good times. They've been together again lately - him, Sammy, Dad - and forgiveness had begun to surface in short fits. The absolution stung like an antiseptic, but it was healing.  Still, Dean doesn't know how Sammy feels. He sometimes thinks that Sam hated their father, and in some ways knows it to be true. Sammy never saw that he did the best he could, which is something that Dean repeats often because sometimes he can't convince himself of the same thing. He wants to believe in his father the same way he did as a child.  Now that he's dead he'll never have the chance.

He feels more anger with what was about to be than sadness over what was.


	7. January 14, 2010

Dean struggles to keep the guilt down, and shame takes up most of the space that grief should fill. He can’t sleep. Though he knows Jo’s parents, or at least the Roadhouse, brought her up in the life, he feels a heavy responsibility for her dogged pursuit of it. He knows she’d always flown a small flag for him and he knew, he swears he _knew_ the night before the failed raid that she wouldn’t be there if not for him. Somewhere he knows he should give her more credit, recognize that she made her own decisions and that they probably had very little to do with some crush on him. Still, self-loathing and arrogance have a way of conspiring to make you blame yourself for others’ free will. His throat tightens at the thought of her bloodied body.

And Ellen, poor damned Ellen. She never wanted this for any of them - certainly not Jo, but not Dean or Sam either. She wanted them to be safe. While she’d never be his mom, no one else had come so close to stitching up that ragged hole in his chest. Save Bobby, no one else had ever particularly cared for his or Sam’s safety; no one else had ever put their children before the job. Ellen had, though. The universe had repaid her dedication with the death of her only child. It killed her to save two orphan boys. They shouldn’t have been there, Dean thinks. His chest hurts. None of them should have.  
  
When at last he drifts off, he wonders if people aren’t beginning to make a habit out of dying for him.


	8. May 12, 2010

There is nothing worse than this. Nothing. Dean is not whole. He is not anything. He can’t pick himself up off his knees. For that one black hole of a moment, he has lost everything. Cas is splattered around him. Bobby is dead on the ground. And Sammy, well. Dean imagines his soul being ripped from his chest. His brother’s limbs torn from his body and sewn back on. For the first time in his life he is utterly convinced that there is no way around this, that he will never see his brother again. The nausea is backbreaking.

He almost regrets it when Cas touches his forehead. Why should he bother living? _If I die I’ll go to Heaven_ , he thinks. Would he know where his brother is, then? Would angels taunt him? That would be worse than Hell, and at least in the Pit he’d be closer to Sammy. He would torture for a millennia to close that distance. Sam wouldn’t want it, though. And Dean promised, swore that he'd keep going. Somewhere in that memory he finds it in himself to push off the ground. He thinks of Sammy’s face. He fights the nausea. He carries on.

Later, when he tries to remember the months that followed, he can barely recall a thing.


	9. April 4, 2011

Moving in with Lisa had not been what Dean expected, if he expected anything. With its stillness and immutable four walls, the permanence was severe. It gave him an uncomfortable awareness of his limbs. He thought that it must be how stable people felt when they’ve been uprooted: that vague sense of panic, the heavy feeling low in their stomachs. He felt like a new orphan, sent to live with a relative he’d only met twice. Someone he loved but wasn’t quite himself around. His grip tightens on the steering wheel at the thought. None of this is to say that he didn’t love Lisa wholly, fiercely. He did and does. It was just uncharted territory.

 Losing her has been more familiar. Dean finds himself contending better with being the driver of the other car, a temporary if damaging presence, than anything constant in her or Ben’s lives. Loss and transience have bordered his entire life and walking away from them was as selfish as it was selfless. Breathing comes easier now. Though he refuses to say it, he feels relieved to have failed them so lightly, divine intervention aside. His conscience is already weighted with Sam’s soul, with all the others for whom Dean’s failure has meant death.

He sighs, eyes focused on the road. At least Lisa and Ben lived through him.


	10. July 8, 2011

Cas disappears in a pool of ink and water. It feels like watching a ship sink to see a vessel, an angel, a god go under like that. Dean knows he lost Cas the second he took those souls into himself, but he’d never stopped hoping to get him back, that they could make things right. Cas had always returned before, whether from Heaven or death - there was no reason he wouldn’t eventually come down off his self-made pedestal, too. The ebb and flow of their relationship felt like an unstated fact in both of their lives and Dean can’t believe that the tide has finally taken him out for good.

A comforting wave of grief settles over him. When the trench coat floats to shore, he picks it up and resists the urge to wrap himself in it. Impracticalities of putting on a wet coat aside, he is uncomfortable with the desire. It makes him feel childish. So he folds it up and puts it in a plastic grocery bag until they get back to Bobby’s, and briefly wonders if he shouldn’t get it dry-cleaned. It would be hard to explain the gruesome stains, he decides, but he does hang it up to dry. It seems important to keep from adding mildew to the blood on the lapels. When they leave he places it back in the trunk alongside shotguns, salt, and an angel blade.

Dean maintains a quiet, steady hope for Cas’ return and does not mourn after that.


	11. January 28, 2012

Bobby was never supposed to die. Of anyone, he wasn’t. He was such a constant in their lives, more than a mentor, than a father figure. He was _Bobby_. When Dean considers it, he wonders if what he feels is shock, or maybe denial. _Denial_ , he thinks, _that’s what it is_. A hollow sensation that is not sadness or anger or grief. Even denial seems distantly close, like a sentence lost behind his teeth. The idea that Bobby could die had sincerely never occurred to him.

Later on, Dean can’t decide if having his ghost around makes things any easier. Everyone’s ghosts have stuck around, in their way. Those of his parents, of Sam and of Cas, of people not completely dead and of people salted and burned. Being able to talk to one softens but does not completely take the edge off the loss, and in some ways makes it worse. It’s still just a specter of the man. He will never be whole. Still, it hurts to think of burning the flask and he knows then that he’s finally in mourning.

The loss makes its notch on Dean’s heart and he takes comfort in the familiar tension in his chest.


	12. July 17, 2012

Dean doesn’t know how long he’s been in Purgatory. The thrum of nervous energy radiating from his sternum has not changed in the days or months or years he’s spent here. It’s impossible to tell; time is different. He is implausibly alone. By the time he meets Benny he is so grateful to hear a voice untainted by malice that he almost collapses. 

The weeks they spend looking for Cas are muddled. Every day is a continual wave of monsters, of phantom hunger and exhaustion. He knows only to keep moving, that each beheading and slice of his machete bring him closer to his friend. Slowly, he learns to count the time by the accumulation of grime on his face and hands. Seven weeks have passed when they find him. Four more pass before he is lost again. Dean has stopped keeping track of how often he fails people, and angels.

He never stops thinking about Cas’ fingers slipping from his grasp.


	13. April 4, 2013

Dean had done everything to get Benny topside. He had sliced and maimed and murdered his way through a wasteland; he had cut open his own arm and taken in Benny’s burnt-out soul, carrying him across the void, and spent four days hitchhiking seventeen hundred miles into back alley wilderness to drip Benny back into himself. He had done _everything_. A grimace hacks across his face at the thought. There are few people in the world that Dean has gone to such lengths for, so few with whom he has shared that kind of trust. So maybe it isn’t so bad, then, that Benny took this hit for him. For Sam.

He tries to tell himself that Benny agreed to it. He wanted to go back to that green-grey place; to what was, in reality, his home. Earth wasn’t meant for things like him - the atmosphere wasn’t quite right; the environment harsh, oppressive, and eventually he would choke. Dean talks himself into this, and is not completely wrong. Benny wouldn’t have been able to cut it much longer. It isn't enough, but it soothes Dean’s guilt. The pain numbs. He feels empty.

Even monsters make sacrifices.


	14. June 2, 2013

Kevin sits at the long table, laptop light illuminating his face. His brow is furrowed and the heel of his hand pushes deep-set wrinkles into his chin. Dean knows that he’s scouring for stories of angels, of confused people in tattered clothes, and that it’s been his mission for several days. He stands and sighs, “Get some sleep, kid,” and waits for Kevin to nod before walking away. He trails his fingers along the wall that leads to Sam’s bedroom and lets them catch on the doorknob, turning it carefully. The creak of the hinges doesn’t wake him and Dean watches the covers rise and fall for a moment before closing the door. He hopes that Sammy isn’t dreaming.

Cas’ new room is just down the hall and Dean treads silently to the open door, tilting his head to look around the frame. Cas lays stretched out on top of all the bedding, stripped down to borrowed undershirt and boxers. Even in sleep, he frowns. For a moment, Dean stands and frowns with him, arms crossed; Cas is hurting, and Dean hurts for him, same as always. Except now, a gentle hope has taken hold in the space where grief and homesickness usually fester, pushing back the lump in his throat and the cresting nausea in his gut. They _survived_. Sam, Cas, Kevin. All of them. He is unaccountably grateful and his chest seems featherlight, weightless. Despite all the tragedy, all the gaping wounds and unaccounted losses, Dean feels safe. They have the bunker, they have each other. Heaven and Hell can wait.

Warmth fills his lungs and he starts toward his own room.


	15. November 2, 2013

_Thirty years._ Dean heaves a sigh and knocks back a swig of his beer. He thinks about carrying Sammy out of the burning house; he thinks about his dad, shouting for him to get outside; he thinks about encounters with ghosts and trips to Heaven and how he has come to know his mom in ways he dreamt of but never bothered hoping for. He stretches, cracking his elbows, and the table is smooth beneath his fingers.

He wonders if she would be proud of him and smirks a little. It’s a silly if not outright embarrassing thought, but as he downs the rest of his beer he allows himself to indulge. She _would_ be proud of how much he’s accomplished, he decides. He’s saved Sammy, kept their family together; he’s clawed his way out of every bad spot from Heaven to Hell and he’s always come out fighting. The empty bottle clinks against a ceramic coaster. Really, he’s come so far. He takes care of himself now, cooks dinner most days and is up to six hours of sleep every night; he drinks more coffee than whiskey. The nightmares have dwindled, and the decades-old ache in his chest is so faint that he can go days without feeling it. She would be proud of him.

Sam turns the corner and pauses, wondering what made Dean smile so broadly.

**Author's Note:**

> Title taken from T.S. Eliot's _Portait of a Lady_ , which can be found [here](http://www.bartleby.com/198/2.html).
> 
> This was mostly a therapeutic exercise, so thanks for sticking around.


End file.
